NPASS Compound

Structure

NPC311246 OpenBabel07101719512D 52 57 0 0 1 0 0 0 0 0999 V2000 1.0563 2.5385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6962 0.8443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2382 1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0006 -0.0422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6807 1.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0388 -4.8301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0388 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8781 3.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9000 2.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7326 -1.0422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1346 0.4578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8666 -0.5422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2685 0.9578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5987 0.4578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9321 3.5405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8666 2.4578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0388 -3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3872 1.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 2.4190 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.5987 -0.5422 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5254 2.6270 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7326 0.9578 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9266 3.4360 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7326 1.9578 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5909 2.0032 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0388 -3.0981 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0006 0.9578 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5388 -2.2321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0388 -1.3660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1346 2.4578 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0388 -1.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8666 0.4578 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2685 1.9578 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0006 1.9578 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7045 -2.5823 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4647 -1.0422 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5958 4.1791 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5987 2.4578 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -2.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5388 -2.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0006 2.9578 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5388 -3.9641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5388 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5388 -2.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5388 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 6 47 1 0 0 0 0 7 48 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 10 12 1 0 0 0 0 10 21 1 0 0 0 0 11 13 1 0 0 0 0 11 29 1 0 0 0 0 12 37 1 0 0 0 0 13 38 1 0 0 0 0 14 21 1 0 0 0 0 14 23 1 0 0 0 0 15 22 1 0 0 0 0 15 24 1 0 0 0 0 16 25 1 0 0 0 0 16 39 1 0 0 0 0 17 40 1 0 0 0 0 18 28 1 0 0 0 0 18 49 1 0 0 0 0 19 26 1 0 0 0 0 20 3 1 1 0 0 0 20 22 1 0 0 0 0 21 41 1 6 0 0 0 22 38 1 6 0 0 0 23 25 1 0 0 0 0 23 37 1 6 0 0 0 24 34 1 0 0 0 0 24 42 1 6 0 0 0 25 43 1 6 0 0 0 26 9 1 1 0 0 0 26 50 1 0 0 0 0 27 17 1 1 0 0 0 27 30 1 0 0 0 0 27 51 1 0 0 0 0 28 31 1 0 0 0 0 28 47 1 1 0 0 0 29 37 1 6 0 0 0 29 39 1 0 0 0 0 30 33 1 0 0 0 0 30 44 1 6 0 0 0 31 32 1 0 0 0 0 31 45 1 6 0 0 0 32 35 1 0 0 0 0 32 48 1 1 0 0 0 33 36 1 0 0 0 0 33 52 1 1 0 0 0 34 38 1 6 0 0 0 34 39 1 0 0 0 0 35 49 1 0 0 0 0 35 52 1 6 0 0 0 36 50 1 6 0 0 0 36 51 1 0 0 0 0 37 4 1 6 0 0 0 38 5 1 6 0 0 0 39 46 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	744.47
Volume:	746.034
LogP:	2.865
LogD:	3.126
LogS:	-3.739
# Rotatable Bonds:	12
TPSA:	196.99
# H-Bond Aceptor:	13
# H-Bond Donor:	7
# Rings:	6
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.153
Synthetic Accessibility Score:	5.968
Fsp3:	1.0
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.525
MDCK Permeability:	0.0001039892085827887
Pgp-inhibitor:	0.956
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.257
20% Bioavailability (F20%):	0.027
30% Bioavailability (F30%):	0.824

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	62.33403778076172%
Volume Distribution (VD):	0.321
Pgp-substrate:	10.604835510253906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.935
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.462
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.006
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.072
CYP3A4-inhibitor:	0.06
CYP3A4-substrate:	0.181

ADMET: Excretion

Clearance (CL):	1.032
Half-life (T1/2):	0.566

ADMET: Toxicity

hERG Blockers:	0.657
Human Hepatotoxicity (H-HT):	0.114
Drug-inuced Liver Injury (DILI):	0.03
AMES Toxicity:	0.082
Rat Oral Acute Toxicity:	0.073
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.94
Carcinogencity:	0.055
Eye Corrosion:	0.004
Eye Irritation:	0.015
Respiratory Toxicity:	0.973

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC311246

Natural Product ID:	NPC311246
*Common Name:**	Halityloside F
IUPAC Name:	(3S,5S,6R,8S,9R,10S,13R,14S,15R,17R)-17-[(2R,5S)-5-[(2R,3R,4S,5S)-4-hydroxy-3-[(2S,3R,4S,5R)-4-hydroxy-3,5-dimethoxyoxan-2-yl]oxy-5-(hydroxymethyl)oxolan-2-yl]oxy-6-methylheptan-2-yl]-10,13-dimethyl-1,2,3,4,5,6,7,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,6,8,15-tetrol
Synonyms:	Halityloside F
Standard InCHIKey:	VLALYUCTTSXBPR-GTWYYQACSA-N
Standard InCHI:	InChI=1S/C39H68O13/c1-19(2)26(50-36-33(30(44)27(17-40)51-36)52-35-32(48-7)31(45)28(47-6)18-49-35)9-8-20(3)22-15-24(42)34-38(22,5)13-11-29-37(4)12-10-21(41)14-23(37)25(43)16-39(29,34)46/h19-36,40-46H,8-18H2,1-7H3/t20-,21+,22-,23-,24-,25-,26+,27+,28-,29-,30+,31+,32-,33-,34-,35+,36-,37+,38-,39+/m1/s1
SMILES:	OC[C@@H]1O[C@H]([C@@H]([C@H]1O)O[C@@H]1OC[C@H]([C@@H]([C@H]1OC)O)OC)O[C@H](C(C)C)CC[C@H]([C@H]1C[C@H]([C@@H]2[C@]1(C)CC[C@H]1[C@@]2(O)C[C@H]([C@@H]2[C@]1(C)CC[C@@H](C2)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446839
PubChem CID:	21674184
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33455	nardoa tuberculata	Species	Ophidiasteridae	Eukaryota	n.a.	Okinawan, Japan	n.a.	PMID[8377014]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
LD50	1
MIC	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	MIC	=	5.0	ug	PMID[451730]
NPT6256	Organism	Sphaerechinus granularis	Sphaerechinus granularis	LD50	=	1.0	10'-6M	PMID[451730]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC311246 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	552
0.1-0.2	4895
0.2-0.3	13278
0.3-0.4	10758
0.4-0.5	5647
0.5-0.6	3797
0.6-0.7	2369
0.7-0.8	993
0.8-0.85	169
0.85-0.9	87
0.9-0.95	140
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC167644
0.9885	High Similarity	NPC113500
0.9885	High Similarity	NPC477224
0.9885	High Similarity	NPC3538
0.9767	High Similarity	NPC473542
0.9767	High Similarity	NPC279329
0.9659	High Similarity	NPC175
0.9659	High Similarity	NPC45959
0.9659	High Similarity	NPC24960
0.9659	High Similarity	NPC252253
0.9659	High Similarity	NPC473774
0.9655	High Similarity	NPC36372
0.9655	High Similarity	NPC5632
0.9655	High Similarity	NPC293609
0.9655	High Similarity	NPC149966
0.9651	High Similarity	NPC82955
0.9556	High Similarity	NPC477222
0.9556	High Similarity	NPC477223
0.9551	High Similarity	NPC473064
0.9551	High Similarity	NPC473067
0.9551	High Similarity	NPC473065
0.9545	High Similarity	NPC144790
0.9545	High Similarity	NPC88962
0.9545	High Similarity	NPC149400
0.9545	High Similarity	NPC277774
0.9535	High Similarity	NPC281004
0.9451	High Similarity	NPC473638
0.9444	High Similarity	NPC139271
0.9444	High Similarity	NPC304011
0.9444	High Similarity	NPC142264
0.9444	High Similarity	NPC476510
0.9438	High Similarity	NPC309866
0.9438	High Similarity	NPC473851
0.9438	High Similarity	NPC253268
0.9438	High Similarity	NPC174024
0.9438	High Similarity	NPC473503
0.9438	High Similarity	NPC179859
0.9438	High Similarity	NPC475436
0.9438	High Similarity	NPC312678
0.9438	High Similarity	NPC291547
0.9438	High Similarity	NPC131693
0.9432	High Similarity	NPC210759
0.9432	High Similarity	NPC204881
0.9432	High Similarity	NPC229801
0.9432	High Similarity	NPC307167
0.9432	High Similarity	NPC473830
0.9425	High Similarity	NPC20822
0.9425	High Similarity	NPC102725
0.9425	High Similarity	NPC473472
0.9419	High Similarity	NPC43912
0.9419	High Similarity	NPC140446
0.9341	High Similarity	NPC233649
0.9341	High Similarity	NPC470028
0.9333	High Similarity	NPC474399
0.9333	High Similarity	NPC92196
0.9333	High Similarity	NPC469710
0.9326	High Similarity	NPC141769
0.9326	High Similarity	NPC297348
0.9326	High Similarity	NPC249204
0.9326	High Similarity	NPC477547
0.9326	High Similarity	NPC234352
0.9326	High Similarity	NPC477451
0.9326	High Similarity	NPC48339
0.9326	High Similarity	NPC325828
0.9326	High Similarity	NPC177834
0.9326	High Similarity	NPC250393
0.9318	High Similarity	NPC65550
0.9318	High Similarity	NPC223143
0.9247	High Similarity	NPC477225
0.9247	High Similarity	NPC475574
0.9239	High Similarity	NPC473616
0.9231	High Similarity	NPC473287
0.9231	High Similarity	NPC121453
0.9222	High Similarity	NPC222731
0.9222	High Similarity	NPC471464
0.9222	High Similarity	NPC294686
0.9222	High Similarity	NPC217205
0.9222	High Similarity	NPC291203
0.9222	High Similarity	NPC30687
0.9222	High Similarity	NPC305418
0.9222	High Similarity	NPC264101
0.9213	High Similarity	NPC476668
0.9213	High Similarity	NPC473637
0.9213	High Similarity	NPC59006
0.9205	High Similarity	NPC131466
0.9195	High Similarity	NPC472396
0.9186	High Similarity	NPC290612
0.913	High Similarity	NPC475207
0.913	High Similarity	NPC307534
0.913	High Similarity	NPC274200
0.913	High Similarity	NPC476112
0.9121	High Similarity	NPC475351
0.9121	High Similarity	NPC473727
0.9121	High Similarity	NPC19400
0.9121	High Similarity	NPC107962
0.9121	High Similarity	NPC206003
0.9121	High Similarity	NPC107188
0.9121	High Similarity	NPC473610
0.9121	High Similarity	NPC211354
0.9121	High Similarity	NPC6295
0.9111	High Similarity	NPC476669
0.9111	High Similarity	NPC137004
0.9111	High Similarity	NPC172838
0.9111	High Similarity	NPC473726
0.9043	High Similarity	NPC476512
0.9043	High Similarity	NPC108227
0.9043	High Similarity	NPC472081
0.9032	High Similarity	NPC473518
0.9022	High Similarity	NPC160426
0.9022	High Similarity	NPC184617
0.9022	High Similarity	NPC103616
0.9022	High Similarity	NPC470865
0.9022	High Similarity	NPC284104
0.9022	High Similarity	NPC470866
0.9022	High Similarity	NPC473601
0.9022	High Similarity	NPC97700
0.9022	High Similarity	NPC237071
0.9022	High Similarity	NPC116756
0.9022	High Similarity	NPC475643
0.9022	High Similarity	NPC296936
0.9022	High Similarity	NPC470863
0.9022	High Similarity	NPC132080
0.9022	High Similarity	NPC238796
0.9022	High Similarity	NPC98018
0.9022	High Similarity	NPC287483
0.9022	High Similarity	NPC128572
0.9022	High Similarity	NPC232037
0.9022	High Similarity	NPC475625
0.9022	High Similarity	NPC30856
0.9022	High Similarity	NPC84111
0.9022	High Similarity	NPC203434
0.9022	High Similarity	NPC195297
0.9022	High Similarity	NPC470864
0.9011	High Similarity	NPC475325
0.8989	High Similarity	NPC228059
0.8977	High Similarity	NPC161928
0.8977	High Similarity	NPC210658
0.8966	High Similarity	NPC273290
0.8966	High Similarity	NPC232044
0.8947	High Similarity	NPC470029
0.8947	High Similarity	NPC114700
0.8947	High Similarity	NPC134967
0.8947	High Similarity	NPC310138
0.8936	High Similarity	NPC470030
0.8925	High Similarity	NPC470862
0.8925	High Similarity	NPC83137
0.8925	High Similarity	NPC51520
0.8925	High Similarity	NPC470861
0.8925	High Similarity	NPC232611
0.8925	High Similarity	NPC115165
0.8925	High Similarity	NPC303069
0.8913	High Similarity	NPC477494
0.8876	High Similarity	NPC128475
0.8854	High Similarity	NPC139181
0.8854	High Similarity	NPC97260
0.8854	High Similarity	NPC476837
0.8851	High Similarity	NPC227260
0.8837	High Similarity	NPC470611
0.8837	High Similarity	NPC296734
0.883	High Similarity	NPC291548
0.8817	High Similarity	NPC156377
0.8804	High Similarity	NPC191915
0.8804	High Similarity	NPC151214
0.8723	High Similarity	NPC470591
0.871	High Similarity	NPC57964
0.871	High Similarity	NPC94582
0.8652	High Similarity	NPC471240
0.8646	High Similarity	NPC476839
0.8646	High Similarity	NPC477172
0.8646	High Similarity	NPC476838
0.8636	High Similarity	NPC474156
0.8632	High Similarity	NPC292775
0.8617	High Similarity	NPC472989
0.8617	High Similarity	NPC252056
0.8605	High Similarity	NPC257296
0.8605	High Similarity	NPC248944
0.8605	High Similarity	NPC7479
0.8571	High Similarity	NPC475521
0.8571	High Similarity	NPC475365
0.8542	High Similarity	NPC41843
0.8526	High Similarity	NPC210157
0.8523	High Similarity	NPC241959
0.8523	High Similarity	NPC470070
0.8511	High Similarity	NPC21897
0.8495	Intermediate Similarity	NPC224003
0.8495	Intermediate Similarity	NPC182740
0.8495	Intermediate Similarity	NPC470623
0.8495	Intermediate Similarity	NPC18724
0.8495	Intermediate Similarity	NPC323231
0.8495	Intermediate Similarity	NPC256104
0.8495	Intermediate Similarity	NPC171741
0.8495	Intermediate Similarity	NPC211845
0.8495	Intermediate Similarity	NPC122083
0.8488	Intermediate Similarity	NPC81074
0.8488	Intermediate Similarity	NPC477282
0.8469	Intermediate Similarity	NPC213190
0.8454	Intermediate Similarity	NPC31346
0.8444	Intermediate Similarity	NPC477283
0.8444	Intermediate Similarity	NPC215968
0.8444	Intermediate Similarity	NPC155531

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC311246 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	527
0.1-0.2	4561
0.2-0.3	2855
0.3-0.4	622
0.4-0.5	309
0.5-0.6	212
0.6-0.7	45
0.7-0.8	16
0.8-0.85	1
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9326	High Similarity	NPD8171	Discontinued
0.8605	High Similarity	NPD6928	Phase 2
0.8384	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD7328	Approved
0.7636	Intermediate Similarity	NPD7327	Approved
0.7589	Intermediate Similarity	NPD8378	Approved
0.7589	Intermediate Similarity	NPD8380	Approved
0.7589	Intermediate Similarity	NPD8296	Approved
0.7589	Intermediate Similarity	NPD8379	Approved
0.7589	Intermediate Similarity	NPD8335	Approved
0.7576	Intermediate Similarity	NPD7991	Discontinued
0.7568	Intermediate Similarity	NPD7516	Approved
0.75	Intermediate Similarity	NPD8294	Approved
0.75	Intermediate Similarity	NPD8377	Approved
0.7442	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD8033	Approved
0.7273	Intermediate Similarity	NPD8133	Approved
0.7111	Intermediate Similarity	NPD1810	Approved
0.7111	Intermediate Similarity	NPD1811	Approved
0.7034	Intermediate Similarity	NPD7507	Approved
0.7	Intermediate Similarity	NPD7319	Approved
0.6881	Remote Similarity	NPD6412	Phase 2
0.6838	Remote Similarity	NPD7503	Approved
0.6778	Remote Similarity	NPD4787	Phase 1
0.6778	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD2687	Approved
0.6778	Remote Similarity	NPD2254	Approved
0.6778	Remote Similarity	NPD2686	Approved
0.6777	Remote Similarity	NPD7736	Approved
0.6757	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6940	Discontinued
0.6667	Remote Similarity	NPD371	Approved
0.6667	Remote Similarity	NPD8174	Phase 2
0.6639	Remote Similarity	NPD6370	Approved
0.6633	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD3669	Approved
0.6632	Remote Similarity	NPD6118	Approved
0.6632	Remote Similarity	NPD6697	Approved
0.6632	Remote Similarity	NPD6115	Approved
0.6632	Remote Similarity	NPD6114	Approved
0.6557	Remote Similarity	NPD8293	Discontinued
0.6526	Remote Similarity	NPD6116	Phase 1
0.6496	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6059	Approved
0.6471	Remote Similarity	NPD6054	Approved
0.6429	Remote Similarity	NPD8449	Approved
0.6421	Remote Similarity	NPD6117	Approved
0.6378	Remote Similarity	NPD8450	Suspended
0.6327	Remote Similarity	NPD7525	Registered
0.6281	Remote Similarity	NPD6015	Approved
0.6281	Remote Similarity	NPD6016	Approved
0.6273	Remote Similarity	NPD1700	Approved
0.626	Remote Similarity	NPD7492	Approved
0.623	Remote Similarity	NPD5988	Approved
0.6211	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.621	Remote Similarity	NPD6616	Approved
0.6179	Remote Similarity	NPD8328	Phase 3
0.6179	Remote Similarity	NPD6067	Discontinued
0.617	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.617	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.616	Remote Similarity	NPD7078	Approved
0.6146	Remote Similarity	NPD3703	Phase 2
0.6146	Remote Similarity	NPD3702	Approved
0.6132	Remote Similarity	NPD8035	Phase 2
0.6132	Remote Similarity	NPD8034	Phase 2
0.6106	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6686	Approved
0.6064	Remote Similarity	NPD4245	Approved
0.6064	Remote Similarity	NPD4244	Approved
0.6058	Remote Similarity	NPD7524	Approved
0.6017	Remote Similarity	NPD8297	Approved
0.6017	Remote Similarity	NPD6882	Approved
0.5984	Remote Similarity	NPD6033	Approved
0.5957	Remote Similarity	NPD3698	Phase 2
0.5957	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.595	Remote Similarity	NPD6009	Approved
0.5948	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD7638	Approved
0.5942	Remote Similarity	NPD7625	Phase 1
0.5941	Remote Similarity	NPD1780	Approved
0.5941	Remote Similarity	NPD1779	Approved
0.5935	Remote Similarity	NPD6319	Approved
0.5922	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD7640	Approved
0.5893	Remote Similarity	NPD7639	Approved
0.5865	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD2267	Suspended
0.5851	Remote Similarity	NPD5360	Phase 3
0.5851	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD4159	Approved
0.5833	Remote Similarity	NPD5777	Approved
0.5833	Remote Similarity	NPD4632	Approved
0.5825	Remote Similarity	NPD6695	Phase 3
0.5812	Remote Similarity	NPD7320	Approved
0.581	Remote Similarity	NPD8308	Discontinued
0.5789	Remote Similarity	NPD7632	Discontinued
0.5778	Remote Similarity	NPD6123	Approved
0.5776	Remote Similarity	NPD7128	Approved
0.5776	Remote Similarity	NPD6402	Approved
0.5776	Remote Similarity	NPD6675	Approved
0.5776	Remote Similarity	NPD5739	Approved
0.5763	Remote Similarity	NPD6373	Approved
0.5763	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD6372	Approved
0.5755	Remote Similarity	NPD7750	Discontinued
0.5743	Remote Similarity	NPD7645	Phase 2
0.5741	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD6700	Approved
0.5729	Remote Similarity	NPD4789	Approved
0.5698	Remote Similarity	NPD887	Approved
0.5698	Remote Similarity	NPD889	Approved
0.5698	Remote Similarity	NPD895	Approved
0.5698	Remote Similarity	NPD894	Approved
0.5688	Remote Similarity	NPD6702	Approved
0.5688	Remote Similarity	NPD6703	Approved
0.5686	Remote Similarity	NPD4748	Discontinued
0.5678	Remote Similarity	NPD6881	Approved
0.5678	Remote Similarity	NPD6899	Approved
0.5667	Remote Similarity	NPD8130	Phase 1
0.5667	Remote Similarity	NPD6650	Approved
0.5667	Remote Similarity	NPD6649	Approved
0.5641	Remote Similarity	NPD6008	Approved
0.5635	Remote Similarity	NPD8515	Approved
0.5635	Remote Similarity	NPD8517	Approved
0.5635	Remote Similarity	NPD8516	Approved
0.5635	Remote Similarity	NPD8513	Phase 3
0.5614	Remote Similarity	NPD8418	Phase 2
0.5607	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.56	Remote Similarity	NPD3701	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data